1-((3a′S,6′R,6a′R)-4′,4′-bis(hydroxymethyl)tetrahydrospiro-[cyclohexane-1,2′-furo[3,4-d]-[1,3]dioxol]-6′-yl)-5-methylpyrimidine-2,4((1H,3H)-dione) | 1191255-81-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-((3a′S,6′R,6a′R)-4′,4′-bis(hydroxymethyl)tetrahydrospiro-[cyclohexane-1,2′-furo[3,4-d]-[1,3]dioxol]-6′-yl)-5-methylpyrimidine-2,4((1H,3H)-dione)
• 英文别名: 2',3'-O-cyclohexylidene-4'-C-hydroxymethyl-5-methyluridine；1-[(3aS,6R,6aR)-4,4-bis(hydroxymethyl)spiro[6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxole-2,1'-cyclohexane]-6-yl]-5-methylpyrimidine-2,4-dione
• CAS: 1191255-81-8
• 化学式: C₁₇H₂₄N₂O₇
• 分子量: 368.387
• InChiKey: HRWRWUVIFDOZLJ-MBNYWOFBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  118
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-((3a′S,6′R,6a′R)-4′,4′-bis(hydroxymethyl)tetrahydrospiro-[cyclohexane-1,2′-furo[3,4-d]-[1,3]dioxol]-6′-yl)-5-methylpyrimidine-2,4((1H,3H)-dione) 在 咪唑 、 copper(l) iodide 、 甲基叔丁基醚 、 碳酸氢钠 、 戴斯-马丁氧化剂 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 74.5h， 生成 1-((3a′S,4′S,6′R,6a′R)-4′-(((tert-butyldiphenylsilyl)oxy)methyl)-4′-((R)-1-hydroxyethyl)tetrahydrospiro[cyclohexane-1,2′-furo[3,4-d]-[1,3]dioxol]-6′-yl)-5-methylpyrimidine-2,4-(1H,3H)-dione
  参考文献：
  名称：

  Alternative Syntheses of (S)-cEt-BNA: A Key Constrained Nucleoside Component of Bioactive Antisense Gapmer Sequences

  摘要：

  Approaches to the synthesis of the constrained 5-methyluracil nucleoside (S)-cEt-BNA, a key "gapmer" unit in a number of biologically relevant antisense oligonucleotides, are described using 5-methyluridine as starting material. In the shorter synthesis, a nine-step linear sequence afforded a O-protected (S)-cEt-BNA consisting of a [2.2.1]dioxabicycloheptane core in 7% overall yield. A competing reaction in an intramolecular cyclization of a tosylate led to a bicyclic oxetane.

  DOI：

  10.1021/jo502320y
• 作为产物：
  描述：

  5-甲基尿甙 在 camphor-10-sulfonic acid 、 碳酸氢钠 、 戴斯-马丁氧化剂 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 20.0h， 生成 1-((3a′S,6′R,6a′R)-4′,4′-bis(hydroxymethyl)tetrahydrospiro-[cyclohexane-1,2′-furo[3,4-d]-[1,3]dioxol]-6′-yl)-5-methylpyrimidine-2,4((1H,3H)-dione)
  参考文献：
  名称：

  Alternative Syntheses of (S)-cEt-BNA: A Key Constrained Nucleoside Component of Bioactive Antisense Gapmer Sequences

  摘要：

  Approaches to the synthesis of the constrained 5-methyluracil nucleoside (S)-cEt-BNA, a key "gapmer" unit in a number of biologically relevant antisense oligonucleotides, are described using 5-methyluridine as starting material. In the shorter synthesis, a nine-step linear sequence afforded a O-protected (S)-cEt-BNA consisting of a [2.2.1]dioxabicycloheptane core in 7% overall yield. A competing reaction in an intramolecular cyclization of a tosylate led to a bicyclic oxetane.

  DOI：

  10.1021/jo502320y

文献信息

• PROCESS FOR PRODUCTION OF ETHYNYLTHYMIDINE COMPOUND USING 5-METHYLURIDINE AS STARTING RAW MATERIAL
  申请人：Hamari Chemicals, Ltd.

  公开号：EP2277878B1

  公开（公告）日：2014-09-17
• PRODUCTION PROCESS OF ETHYNYLTHYMIDINE COMPOUNDS FROM 5-METHYLURIDINE AS A STARTING MATERIAL
  申请人：Sato Tatsunori

  公开号：US20110054164A1

  公开（公告）日：2011-03-03

  The present invention provides a process for producing 2′,3′-didehydro-3′-deoxy-4′-ethynylthymidine, which is useful as a medicine, in an efficient and industrially advantageous manner, and more specifically, provides a process for producing 2′,3′-didehydro-3′-deoxy-4′-ethynylthymidine as shown below. (wherein R 1 and R 2 independently represent a protective group for a hydroxy group, or R 1 and R 2 together form a protective group for two hydroxy groups, R 3 and R 4 independently represent a protective group for a hydroxy group, R 5 represents a protective group for a hydroxy group, R 6 represents a protective group for a hydroxy group, X represents a leaving group, and Y represents a halogen atom.)
• US8445669B2
  申请人：——

  公开号：US8445669B2

  公开（公告）日：2013-05-21
• Alternative Syntheses of (<i>S</i>)-cEt-BNA: A Key Constrained Nucleoside Component of Bioactive Antisense Gapmer Sequences
  作者：Juan C. Salinas、Michael T. Migawa、Bradley L. Merner、Stephen Hanessian

  DOI：10.1021/jo502320y

  日期：2014.12.5

  Approaches to the synthesis of the constrained 5-methyluracil nucleoside (S)-cEt-BNA, a key "gapmer" unit in a number of biologically relevant antisense oligonucleotides, are described using 5-methyluridine as starting material. In the shorter synthesis, a nine-step linear sequence afforded a O-protected (S)-cEt-BNA consisting of a [2.2.1]dioxabicycloheptane core in 7% overall yield. A competing reaction in an intramolecular cyclization of a tosylate led to a bicyclic oxetane.